Starting my start-up career at Zillow (see this for some perspective) was a very good and very bad pre-cursor for my entrepreneurial journey over the past few years.

It was great in the fact that I now KNOW building a technology business at massive scale is possible; I’ve seen it done from the inside. Most people seriously question whether building something that reaches millions of consumers is possible, because they haven’t seen it with their own eyes

It was bad in the fact that, prior to starting my own company

I thought start-ups were easy. As an employee at Zillow, sure there were challenges, but from my perspective there was never any real risk the company wouldn’t succeed. That’s why I took a personal loan when I left in 2010 to buy my options; I knew there was basically zero chance I’d end up on the short end of the stick (and I didn’t). Of course, Zillow’s not the average start-up. Most start-ups don’t have $6 million in funding pre-launch, a team of 50+ without having shipped a product, or a founder with a multi billion dollar company that transformed an entire industry under his belt.

I talk to founders in the real estate industry on a weekly basis. Most find me via this blog, though I meet some via friends or inside communities I belong to.

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They seek product feedback and strategy. They want to know about problems and incentives for agents as well as consumers. They are looking to get a handle at how to gain adoption, traction, and partnerships in this massively complex and wide-reaching industry we operate in.

Many have no prior history in the industry. Others were agents at one time or another. Still others grew up in a real estate family.

I’ve seen 10 years of what has worked, and what hasn’t. When I hear a pitch or play with a product, I tell it how I see it, regardless of whether that’s what the founder wants to hear. Sometimes, it doesn’t validate their strategy.

“Some don’t like the brutal honesty. Others love it.”

I’ll be honest, I often hate that I now look at every website/app (aka business) from an investor perspective as a result of being peppered with questions for the last few years about Oh. Hey World / Horizon.

Investors are a skeptical bunch because real dollars are at play and there is no sense throwing them down a hole they can never climb out of. They want to under stand your thought process.

I’m skeptical when I speak to founders, on purpose. It doesn’t impress me anymore that someone can build a product. That’s the minimum bar to build a start-up; table stakes. Having a number of people in your trusted circle say “oh yea, that’s a great idea, I would use it” – doesn’t mean anything to me.